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Synthesis, Cell-Surface Binding, and Cellular Uptake of Fluorescently Labeled Glucose−DNA Conjugates with Different Carbohydrate Presentation

AuthorsUgarte-Uribe, Begoña; Pérez-Rentero, Sonia; Lucas, Ricardo CSIC ORCID; Aviñó, Anna CSIC ORCID; Reina, José J. CSIC ORCID; Alkorta, Itziar; Eritja Casadellà, Ramón CSIC ORCID ; Morales, Juan C.
DNA conjugates
Issue Date30-Jun-2010
PublisherAmerican Chemical Society
CitationBioconjugate Chemistry 21(7): 1280-1287 (2010)
AbstractOligonucleotide conjugates carrying carbohydrates at the 5′-end have been prepared. Glucose, fucose, and saccharides containing glucose at the nonreducing end were attached to DNA strands using the classical phosphoramidite chemistry. Two types of spacers and a dendron scaffold helped to obtain a diversity of sugar presentations in the DNA conjugates. Cellular surface adsorption and cellular uptake of carbohydrate oligonucleotide antisense sequences were measured using flow cytometric analysis. Conjugates with the glucose moiety linked through long spacers (15 to 18 atom distances) were internalized better than those with short linkers (4 atom distance) and than DNA control strands without sugar modification. Conjugates with tetravalent presentation of glucose did not improve cell uptake.
Description8 páginas, 5 figuras
Publisher version (URL)http://dx.doi.org/10.1021/bc100079n
Appears in Collections:(IIQ) Artículos
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